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Sullivan has played the scenarios over hundreds of times. During four decades with Chicago police, he helped design security plans for countless big events, ranging from sports championships, to the 1996 Democratic Convention, and President Obama's 2008 victory rally in Grant Park.

"Our citizens today are the ultimate force multiplier," he says, noting that in a long un-secured area like a parade route, police can't see everything, but often, citizens will.

"If you had a trash container and you see a fellow with a backpack and all of a sudden the individual abandons it and puts it into a garbage can....a perfectly good backpack in a garbage can?"

He urges citizens at such events not to be shy.

"If you saw somebody put a backpack down and just walk, stroll away, say 'Sir, sir, you forgot your backpack!' If that individual ignores you, get a good look at him from head to toe, and look immediately for somebody from public safety," Sullivan advised.

Now a private security consultant, Sullivan makes clear he was not a fan of tight venues like the 2010 Blackhawks victory rally at Michigan and Wacker or the White Sox party five years earlier at LaSalle and Wacker.

This year's event will be held on Hutchinson field at the south end of Grant Park. It's a wide but confined space, which will have only two entrances.

"They're following the same model that we used in 2008 for the Obama rally," he says. "basically it's an easy venue to secure for a public event, because there's limited streets to it."

Sadly, everything has to be taken into account. And with that in mind, organizers know that the Grant Park site is also much easier to evacuate than the previous spots on Wacker Drive.

"If something were to happen, the crowd is going to be able to move, and move more freely," he says. "Because there's unlimited areas they can escape to."